


In Which Anna Meets Dean

by melodytran



Category: Supernatural
Genre: Alternate Universe - High School, Destiel - Freeform, Established Relationship, F/F, Fluff, M/M, POV Third Person, idk - Freeform, not really destiel but it is
Language: English
Status: Completed
Published: 2014-11-10
Updated: 2014-11-10
Packaged: 2018-02-24 19:37:46
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,277
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2593817
Author URL: https://archiveofourown.org/users/melodytran/pseuds/melodytran
Summary: <blockquote class="userstuff">
              <p>Cas has a boyfriend named Dean, who is a lot hotter than Anna expected. He also has a friend named Charlie, who is a lot hotter than Anna expected. In other words, she really needs to increase her standards.</p>
            </blockquote>





	In Which Anna Meets Dean

Anna Milton and Castiel Novak were best friends since Pre-K, all the way up to their senior year of high school. Even though they had their own group of friends, and were always busy (either going to the mall or studying or something of that sort), they ate lunch together every single day and told each other everything. They had a rule, and that rule meant that neither of them would ever keep something a secret from the other. Not under a single circumstance. Except for one.

But Anna was skilled at prying into other people's business, especially when she wasn't supposed to. That was how Anna came to know about Dean Winchester.

It started a year ago, way back during her junior year of high school, when Cas was on his phone during class. That was the first signal that something was going on- Cas never broke the school rules. Maybe during lunch, sure, but Castiel always paid utmost attention in their AP Biology class. For good reason, too, considering their teacher, Mrs. Tran, was terrifying when angry.

Anna had stared at him for ten solid seconds before she recollected her wits. Then, with a sudden jolt, she realized he was texting someone. Not that he didn't have a social life, but (to be frank) he really didn't have a social life.

"Who are you texting?" Anna had whispered as innocently as possible. Cas acted like he hadn't heard her. Or maybe he really hadn't heard her. Then, Castiel smiled- that rare smile that lit up his eyes and made him seem impossibly in love. The gooey, annoying, romantic comedy sort of thing. And then it had hit her.

She repeated her question, and poked him in the arm with a pencil.

"A friend," he whispered back. "Now be quiet before Mrs. Team notices." Anna sank back into her seat.

Yeah, right. A friend my ass, Anna was tempted to say. She didn't say that though, mostly because Mrs. Tran shot her the evil eye. After five minutes of taking notes and waiting until Mrs. Tran's back was turned, Anna had returned her attention to Castiel.

"And what's your friend's name?" she had asked, leaning over, thus resulting in Castiel attempting to hide the phone behind his back.

"Dean. Dean Winchester."

* * *

 

Now, there she was, picking at her school lunch eight months later and two weeks before summer break. Cas had later told her Dean was his boyfriend, not that she hadn't known already. She was a little upset as he broke the "no secret's" rule. No, not rule. To her, it might as well have been God's fucking law.

Anna had never actually seen Cas's boyfriend, and since she was Cas's best friend, this pissed her off to no end. She pictured Dean, however, nerdy but lowkey rebellious kind of person- someone similar to Cas. She also pictures him as a total gentleman because if he wasn't, she was totally prepared to kick his ass. Her and Gabriel both.

Anna took a slow bite of her veggie lasagna which tasted more like cardboard than anything else. American school lunches were always, and will always be, absolute shit.

"Cas, you can come over to work on that project for Mrs. Wesson at my place after school, right? I mean, unless you've got other stuff planned," Anna said, despite knowing that Cas almost never had anything planned. And since it was a Tuesday there should've been nothing else to do but apparently her English teacher wanted to make her last two weeks of school as difficult as possible.

"Dean's picking me up from school today for a date, so I can't," Cas murmured apologetically. "Sorry, Anna." Anna gaped at him, her mouth hanging wide open like a goldfish.

"So.... Can I meet you boyfriend?" she said after a beat, twirling her plastic fork and staring at Cas, waiting for his response. He shrugged.

"I guess so."

Anna sat on her hands to keep her from fist-pumping the air.

* * *

Anna scowled as she stared at the clock. Only seventeen minutes left.

She stared at the clock some more. Sixteen minutes left. Breathe, Anna. In and out. In and out. Just sixteen minutes left.

This was taking too long.

Anna ran her finger through her hair and glared at the teacher as he droned on and on, as if it was Mr. Henrikson's fault school wasn't over yet. She tapped her finger irritably on her desk. She began doodling all over her notes, until every last inch of her loose-leaf paper was covered with tiny flowers and a rather rude caricature of her teacher. Thank God she was sitting near the back of the room, or else Mr. Henrikson would have been thirsty for her blood.

Thirteen minutes left.

Mr. Henrikson started passing out worksheets. Anna stared at the first question and buried her face in her hands. School could not be over fast enough, and not just because of Dean Winchester.

She concentrated on the worksheet. After solving twenty two (out of thirty nine) questions, the bell started to ring. It took every ounce of her willpower to not jump up and scream Hallelujah. She was one of the first people out the door. The crowd of students spilled out into the waiting area for the buses. Anna craned her neck over the students, squinting in the brilliant sunlight and looking for Castiel.

Anna spotted him after a minute. He was leaning against the brick walls, texting rapidly on his phone.

"Cas!" she exclaimed, hurrying over to him. He looked up and smiled. Halfway there, she stopped.

Anna had just spotted possibly the most attractive human being in the universe. He was standing awkwardly by the buses. Anna was positive she'd never seen him before, and she knew everyone at Kripke High.

The boy had blondish hair and bright green eyes noticeable from even a distance and freckles. Never did Anna ever think she'd describe freckles as sexy but _damn_. He was wearing a leather jacket and looked indecently attractive. She was having a mini debate in her head on whether to approach the hottie, or keep going to Cas. She decided on the latter.

The guy started walking almost as soon as she did, heading towards the same direction. Anna felt her heart flutter slightly, even though the guy was a total stranger.

Cas nodded at her, and walked past her towards Freckles. Anna watched horror-struck, in the way someone would watch a car crash, as Cas approached the hottie. She could barely make out snippets of their conversation. She watched, with an expression that would be downright comical in any other situation, as Cas smiled and leaned in and suddey they were kissing. Despite her best efforts, a tiny "aw" escaped Anna's mouth.

Centuries later, they pulled apart, Cas grinning like crazy and Dean (as Anna had finally put two and two together) with a mirrored expression, and staring at him with a love-struck look on his face that seemed to just embarrass Cas even more. Anna walked over to the couple.

"Hey, Anna," said Cas. "Um... this is my boyfriend, Dean."

"Castiel Novak," Anna started, letting her annoyance seep into the name like poison. She leaned her head back and close her eyes. She took a few deep breaths to calm herself down, and opened her eyes again just as Cas raised his eyebrows and frowned. She only used his full name when she was either mad or annoyed at him, and he couldn't see why she would be either. "I am so mad at you right now."

"What did I do?" asked her best friend without an ounce of defensiveness in his voice, just plain curiosity. Dean had his fingers entwined with Cas's, and it looked so. Damn. Cute.

"Why didn't you ever think to mention the fact that your boyfriend's _hot_?!"

* * *

 A month later, Anna was peering at Cas over the top of her book (Harry Potter & The Order Of The Pheonix- and if anyone dared to tell her she was too old to read the series, she would have murdered them remorselessly). He was texting. Again. Not that she could blame him- if she had a boyfriend that attractive, she'd be texting him 24/7 the day. "What is it about you that you can't stop texting Dean for ten seconds?" she asked. "Or are you sexting him? Because that I totally understand." Cas choked on his mug of overpriced coffee and set it down on the table.

"Will you stop that?" he asked, face turning as red as her hair.

"Hey, look! We match!" Anna teased. After the small incident at school, she couldn't resist making fun of him sometimes.

"Why am I even friends with you?" asked Cas. Anna grinned.

"Because reasons."

"This is why you're not on the debate team."

"What? I would totally annihilate any opponent I'd go against," Anna said seriously. Her straight expression lasted only five seconds.

"Actually, debate requires brains," he said, looking up from his phone and pocketing it.

"Such harsh words," Anna gasped, clutching her chest with both hands dramatically. "Hey, do you wanna go to the movies this afternoon? I've been dying to see the new Captain America-"

"Actually, I was already going, but with-"

"Dean."

"Yes."

Anna sighed. "Okay. I'll ask Hannah, then." She buried her face in her hands, and sighed again, just in case. Castiel rolled his eyes exaggeratedly.

"Fine. You can come with us," he said. Anna brightened immediately.

"Really? Great!" the redhead exclaimed. "Come on, let's go. Oh, and no making out during the movie. PDA is gross- I don't care if you're my best friend or not."

Cas sighed and sent a quick text to Dean when Anna wasn't looking.

_C: annas coming too. that ok?_

_D: sure, why not? + mind if i drag charlie along._

_C: awesome. there a chance we can set those 2 up?_

_D: idk. theyre both equally annoying. on another note, shall we continue? ;)_

_C: pretty sure annas watching over my shoulder so no._

_D: :( ok. c u in 15. love you_

_C: love you too, bye_

* * *

After the movie, and a series of what seemed like coincidences, Anna found herself hanging out with Charlie- who was an unbelievably lively and nice person. They became good friends in a matter of no time.

On August 27, exactly one week before school started, they went to a nearby Starbucks. Per usual, their conversation approached even the most absurd topics, ranging from a K-drama featuring vampire attorneys to the effectiveness of coke and mentors as a source of energy. The widespread topics they discussed lead to a slew of ridiculous inside jokes and a steadily growing friendship.

That day, the conversation had drifted towards Dean and Cas- or, as Charlie called them, Destiel. (Anna personally thought it would make more sense for them to be called Deastiel but she, apparently, was not the one who called the shots when it came to certain things).

"How did they even get together?" Anna asked, taking a sip of her frappe. "Do you know?"

"Actually, I got them together," Charlie said triumphantly. Anna raised an eyebrow, telling her silently to explain. "Okay. So, Dean and I go to the Campbell's High, which is probably the lamest name for a school ever. I knew Cas because we went to the same church. You know, Garrison? It's like, two blocks away from here. So Cas and I managed to become... well, not friends, but acquaintances. Or something like that. I was friends with Dean since seventh grade, and he was... well, he was as straight as his rainbow slinky."

Anna burst out laughing at that, and Charlie smiled. "Sorry, go on," she said, grinning into her drink. "I'm still listening."

"If you insist. Anyways, being the amazing friend that I am, I did everything in my power to get them together. Sam helped. Sam is Dean's younger brother, in case you don't know." Anna did know, but she didn't say anything. "We did everything. I mean, everything. We even went so far as to locking them in Sam's mom's closet for two hours like we were in middle school. Yeah. But by the end of the summer, right before our junior year started, I was losing all faith in humanity. I went to this very Starbucks, and pretty much walked in on those two making out. Turns out those bastards were dating for an entire month without telling me," Charlie finished.

"So technically speaking, you didn't bring them together," Anna said. Charlie made a face.

"Shut it, Milton. What I say goes." Anna laughed. "Besides, I did introduce them to each other!"

"Touchy."

"Yeah, well, it wasn't really all smooth sailing from there. And it's not like they were those super gooey couple you see on television-"

"Wait, they aren't? Since when?"

Charlie made another face and continued talking as if she hadn't interrupted, "-so I'm pretty sure I can say that I can." Anna nodded. "And besides, why else would he try and return the favor it I hadn't?"

"What?"

"Well, just saying, I have a feeling Dean didn't make me go to that movie with him- the one he was really looking forward to watching with Cas alone- if he didn't have some ulterior motive. He's surprisingly see through." Anna felt all of her blood rushing to her face. "What? I do have a point, you know."

"Shut up."

"See, being good friends with Cas, I know 'shut up' really means 'I love you.'"

Anna didn't try to correct her. Charlie took that as a win.

**Author's Note:**

> Please leave kudos/comments for this attention-craving person. Seriously, comments (especially constructive criticism) is highly appreciated!


End file.
